Outside Sales Manager

Brightside Windows | Chicago, IL

Brightside Windows is one of the fastest-growing residential window companies in the country, operating in 20+ markets and continuing to expand nationwide.

We are currently building and scaling our Chicago market and are looking for a proven Outside Sales Manager with strong door-to-door (D2D) experience to lead from the front and develop a high-performing residential canvassing team.

This is a hands-on leadership role for someone who knows how to recruit, train, motivate, and drive production in the field — not from behind a desk.

If you’ve successfully built D2D teams and want the opportunity to grow with a rapidly expanding company, we want to talk to you.

What You’ll Do

• Build, lead, and develop a high-performance residential canvassing team
• Recruit, hire, and onboard motivated sales representatives
• Set and manage daily, weekly, and monthly production goals
• Conduct ride-alongs and in-field coaching to improve performance and closing rates
• Track KPIs and hold team members accountable to results
• Create a competitive, disciplined, and winning sales culture
• Work directly with ownership to help grow and scale the Chicago market

This role requires a leader who is active in the field, leads by example, and raises the standard every day.

What We’re Looking For

• Proven door-to-door (D2D) sales experience — REQUIRED
• Sales management or team leadership experience — REQUIRED
• Strong residential or in-home sales closing background
• Ability to coach, motivate, and develop salespeople
• Competitive mindset with strong self-discipline and accountability
• Growth-oriented leader who thrives in fast-paced environments

Requirements

• Valid driver’s license and reliable transportation — REQUIRED
• Ability to work evenings and weekends
• Comfortable working outdoors and canvassing neighborhoods

Compensation & Growth

• Performance-based compensation structure (team overrides + commission)
• Successful managers average $20,000–$30,000+ per month
• Uncapped earning potential
• Clear advancement opportunities as Brightside continues expanding into new markets nationwide

If you’re ready to take ownership of a growing market, build a winning team, and grow with a company on the rise, apply today and join Brightside Windows’ continued expansion.

Job Type: Full-time

Pay: $100,000.00 - $165,000.00 per year

Work Location: In person